ELECTROCHEMICAL OXIDATION OF PROLINE DERIVATIVES - TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C

被引：84
作者：
BARRETT, AGM [1 ]
PILIPAUSKAS, D [1 ]
机构：
[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 08期
关键词：
D O I：
10.1021/jo00008a040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The influence of structure on the efficiency of the electrochemical C-5 oxidation of (2S,4S)-hydroxyproline carbamate esters is presented. Optimum methoxylation was observed with (2S,4S)-4-acetoxy-1,2-pyrrolidine-dicarboxylic acid 2-methyl 1-(2-(trimethylsily)ethyl) ester (19). The corresponding C-5 methoxy derivative 20 was converted into bulgecinine (4) via a stereospecific radical homologation to incorporate the C-5 hydroxymethyl substituent. Bulgecin C (1c) was prepared via a beta-stereoselective glycosidation reaction using a 2-azido-2-deoxy-alpha-D-glucopyranosyl trichloroacetimidate derivative, regiospecific C-4' sulfation, and deprotection.
引用
收藏
页码：2787 / 2800
页数：14
相关论文
共 44 条
[21]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[22]  
NASHED MA, 1976, TETRAHEDRON LETT, P3503
[23]   AN EFFICIENT ROUTE TO 1,3-AMINO HYDROXYL SYSTEM VIA ELECTROPHILIC LACTONIZATION OF 2-AMINO-4-PENTENOIC ACID-DERIVATIVES - STEREOSELECTIVE SYNTHESIS OF (-)-BULGECININE [J].
OHFUNE, Y ;
HORI, K ;
SAKAITANI, M .
TETRAHEDRON LETTERS, 1986, 27 (50) :6079-6082
[24]   STEREOSELECTIVE HYDROXYLATION OF N-CARBAMOYL-L-PYROGLUTAMATE - SYNTHESIS OF (-)-BULGECININE [J].
OHTA, T ;
HOSOI, A ;
NOZOE, S .
TETRAHEDRON LETTERS, 1988, 29 (03) :329-332
[25]   A CONVENIENT AND HIGHLY CHEMOSELECTIVE METHOD FOR THE REDUCTIVE ACETYLATION OF AZIDES [J].
ROSEN, T ;
LICO, IM ;
CHU, DTW .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (07) :1580-1582
[26]  
RUSSELL GA, 1985, TETRAHEDRON LETT, V26, P4975
[27]   SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .57. AN EFFICIENT APPROACH TO STEREOSELECTIVE GLYCOSYLATION OF CERAMIDE DERIVATIVES - USE OF PIVALOYL GROUP AS A STEREOCONTROLLING AUXILIARY [J].
SATO, S ;
NUNOMURA, S ;
NAKANO, T ;
ITO, Y ;
OGAWA, T .
TETRAHEDRON LETTERS, 1988, 29 (33) :4097-4100
[28]  
SCHINZER D, 1988, SYNTHESIS-STUTTGART, P263
[29]   RECENT DEVELOPMENTS IN THE SYNTHESIS OF GLYCOCONJUGATES [J].
SCHMIDT, RR .
PURE AND APPLIED CHEMISTRY, 1989, 61 (07) :1257-1270
[30]   FACILE SYNTHESIS OF ALPHA-O-GLYCOSYL AND BETA-O-GLYCOSYL IMIDATES - PREPARATION OF GLYCOSIDES AND DISACCHARIDES [J].
SCHMIDT, RR ;
MICHEL, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1980, 19 (09) :731-732
12345